Hydrogen Peroxide → 4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butan-1-ol
Reaction equation
B1C2CCCC1CCC2.[CH2:10]([C:14]1[C:15]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:21][S:20][C:16]=2[N:17]=[CH:18][N:19]=1)[CH2:11][CH:12]=[CH2:13].[OH-:30].[Na+].OO>O1CCCC1.C(OCC)(=O)C.C(O)C>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[C:15]3[C:14]([CH2:10][CH2:11][CH2:12][CH2:13][OH:30])=[N:19][CH:18]=[N:17][C:16]=3[S:20][CH:21]=2)=[CH:28][CH:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
9-BBN (0.236 g, 0.00193 mol) in tetrahydrofuran (5.00 mL) was treated with 4-but-3-en-1-yl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (0.500 g, 0.00176 mol) in tetrahydrofuran (3.0 mL) at 50° C. for 1 h. Ethanol (1.0 mL), 6 N sodium hydroxide (0.33 mL) and 30% hydrogen peroxide (0.67 mL) were then added successively and the resulting mixture was maintained at 50° C. for 1 h. The reaction was then cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with sodium bicarbonate (2×30 mL). The organic layers were combined, concentrated and purified by column chromatography over silica gel (using ethyl acetate/hexane 1:5-1:1 as an eluent) to afford 4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butan-1-ol as a white solid in 47% yield.
Workup
- temperatureThe reaction was then cooled to room temperature
- washwashed with sodium bicarbonate (2×30 mL)
- concentrationconcentrated
- custompurified by column chromatography over silica gel (
Sources & evidence
- ORD record
- ord-55717429aca24150a1b8c20162f02011
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576080B2
Reaction notes
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